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Coptisine
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Name

Coptisine

 EINECS N/A
CAS No. 3486-66-6 Density g/cm3
PSA 40.80000 LogP 2.80780
Solubility N/A Melting Point 212-217 °C
Formula C19H14 N O4 Boiling Point °Cat760mmHg
Molecular Weight 320.324 Flash Point °C
Transport Information N/A Appearance N/A
Safety A poison by ingestion. When heated to decomposition it emits toxic vapors of NOx. Risk Codes  A poison.:;
Molecular Structure Molecular Structure of 3486-66-6 (COPTISINE) Hazard Symbols A poison.
Synonyms

Berbinium,7,8,13,13a-tetradehydro-2,3:9,10-bis(methylenedioxy)- (8CI); Alkaloid A, fromCoptis groenlandica; Coptisin; Coptisine; YHL II

Article Data 6

Coptisine Synthetic route

C19H15NO5

3486-66-6

coptisine

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h;74%
2086-83-1

berberine

3486-66-6

coptisine

Conditions
ConditionsYield
Multistep reaction;
75-09-2

dichloromethane

2,3,9,10-tetrahydroxy-protoberberine chloride

3486-66-6

coptisine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 40 - 90℃; for 5h; Inert atmosphere;
130-86-9

protopine

3486-66-6

coptisine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: oxalyl dichloride / chloroform / 1 h / Reflux
2: dimethyl sulfoxide / 25.5 h / 115 - 120 °C
View Scheme
20105-28-6

N-Methyl-dihydrocoptisinium-Kation

3486-66-6

coptisine

Conditions
ConditionsYield
In dimethyl sulfoxide at 115 - 120℃; for 25.5h;
53777-78-9

Dihydrocoptisine

3486-66-6

coptisine

Conditions
ConditionsYield
With iodine; potassium acetate In ethanol at 20℃; Inert atmosphere;5.5 mg
94143-83-6

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

3486-66-6

coptisine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve
2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere
3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

C20H16BrNO4

3486-66-6

coptisine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
5: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme
72744-54-8

5-bromo-benzo[1,3]dioxole-4-carbaldehyde

3486-66-6

coptisine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve
2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere
3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere
4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

C20H17NO4

3486-66-6

coptisine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve
2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere
3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere
4: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere
View Scheme

Coptisine Chemical Properties

Product Name: Coptisine
Synonyms of Coptisine (CAS NO.3486-66-6) : [1,3]Benzodioxolo[5,6-a]-1,3-benzodioxolo[4,5-g]quinolizinium, 6,7-dihydro- ; 6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoléin-5-ium  ; Bis[methylenedioxy]protoberberine ; 6H,7H-[1,3]dioxolo[5,4-g][1,3]dioxolo[5'',4'':7,8]isoquino[3,2-a]isoquinolin-5-ium
Product Categories: Alkaloids
CAS NO: 3486-66-6
Molecular Formula:C19H14NO4
Molecular Weight :320.3182
Molecular Structure :

Coptisine History

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). Famous for the bitter taste that it produces, Also found in Greater Celandine and has also been detected in Opium.

Coptisine Uses

 Coptisine (CAS NO.3486-66-6)  is used in Chinese herbal medicine along with the related compound berberine for treating digestive disorders caused by bacterial infections.

Coptisine Toxicity Data With Reference

1.    

orl-rat TDLo:0.1 mg/kg

     BIPBU*    Biological & pharmaceutical bulletin. 24 (2001),1277.

Coptisine Safety Profile

A poison by ingestion. When Coptisine (CAS NO.3486-66-6) is heated to decomposition it emits toxic vapors of NOx.

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